Hermann eritzsche



fonic acids containing into azodyestufi's by the ATENT @FFTQE.

HER-MANN FRITZSGHE, OF BASEL, SWITZERLAND, ASSIGNOR T0 SOCIETY OF CHEMICAL INDUSTRY IN BASLE, 0F BASEL, SWITZERLAND.

.AZD DYESTUFFS DYEING MORDANTED GBOLDS.

No Drawinx: I

To all whom it may concern:

Be it known that I, HERMANN FR rzsoHn, a citizen of the Swiss Republic, and resident of Basel, Switzerland, have invented new Azo Dyestufi's Dyeing Mordanted Goods, of which the following is a full, clear, and exact specification.

I have foundithat new azodyestufi's dyeing mordanted goods can be derived from the diazotationproducts of the arylarnids, of the amino'oxyarylsulfonic acids containing the amino group in a position ortho relativelyto the hydroXyl group and being eventually substituted in the arylamid radical by other substituents, as, for lnsta-nce, amido-, hydroXyL, sulfoor carboxyl groups, that is to say correspond to the general formula wherein X and R stand for aryl-radicals, which may be further substituted.

The aryli'ds of amino-orthooxyarylsulfonic acids and their derivatives corresponding to the above formula can be obtained by acting on the chlorids of halogennitroarylsulthe nitro group in relatively to the halogen or their nitro-, carboXy-,

position ortho with arylamins sulfoor oXycarboXy-derivatives or the like,

substituting a hydroxyl group for the halogen in the condensation products thus obtained by acting thereupon with alkalis, and by reducing the resulting nitrooxy bodies.

The preparation of the parent materials employed for the production of the new azodyestufls is illustrated by the following Examples 1 and 2 and their transformation following Examples 3 to 5.

Emamplc 1. Preparation of the Loony-2- of hydrochloric acid.

aminobenzene i-sulfanild.

sulfochlorid. The liberated hydrochloric acid is neutraiized by addition of chalk in such a quantity that no acid reaction occurs.

Specification of Letters Patent.

Application filed June 7, 1918.

After 2 hours the solution, in which the condensation product is suspended in the form of a thick oil, is heated to boiling and acidified with hydrochloric acid in order to eliminate the chalk in excess and the liquid is decanted from the oil which concretes quickly. By saponification with soda lye and reduction with sodium sulfid according to the method specified in Example 1, the 1- oxy-2-aminobenzene-a-sulfanilid is obtained and can be isolated easily in the form of its hydrochlorid.

In this eXample the anilin can. be replaced by equivalent quantities of its alkyl--, carboxyh, 'sulfoand hydroXy-derivatives and thus the corresponding methylphenylamid, sulfophenylamid, oxycarboxyphenylamid, etc, maybe obtained.

Example 2. Preparation of the terminop/zenyZa-mz'd of the Q-amimoJ-ozvybcnzene- 4-sulfom'c acid. l

138 gr. of paranitranilin are suspended in 2000 cam. of water and in the courseof 1 hour 255 gr. of l-chloro-2-nitrobenzene-4- sulfochlorid are added at 80 to 95 6., the hereby produced hydrochloric acid being neutralized by adding soda lye. After heat ing for 4 hours the mass is acidified with hydrochloric acid and filtered. The residue is saponified by boiling it for 4 hours with an aqueous solution of 120 gr. of soda lye, whereafter the saponified condensation product is precipitated by adding hydrochloric acid. In order to reduce both of the nitro groups the product is treated with sodium sulfid. From the hydrochloric solution the e-aminophenylamid of the 2-aminol-oxybenzene--sulfonic acid is precipitated by addition of sodium carbonate.

Emample 5.

made weakly alkaline with sodium carbonate and the solution of dyestufi is sepa-- rated from calcium sulfate by filtration. From its solution the dyestuff is separated by neutralization and precipitation with common salt. It corresponds to the formula SOaH 'SOgH.

cnnNH-so/ In the form of its sodium salt, the dye- Example 4.

32.3 parts of koxy-3-carboxyphenylamid of the 2-amino-l-oxybenzene l-sulfonic acid are diazotized in the usual manner and the diliicultly soluble yellow-diazo compound obtained is added to a solution of 15 parts of betanaphthol in 13 parts of soda lye of 30 per cent, made alkaline with sodium carbonate. The dyestuif is isolated in the usual manner.

lts sodiunr salt constitutes a dark red powder dissolving in water and in concentrated sulfuric acid to red solutions and dyeing wool in an acid bath Bordeaux-red tints turning by subsequent chromating to a violet very fast to washing, fulling and potting and to light.

the 2 amino-l oxybcnzene- 4 sulfonic acid (prepared according to Example 3) are tetrazotized with parts of hydrochloric acid of 30 per cent. and 14.4 parts of sodium nitrite and the resulting solution of tctrazo body is poured into a solution of 25.4 parts of 1-sulfophenyl3-methyl-5-pyrazolone in 500 parts of water and 20 parts of crystalized sodium acetate. After 2 hours the intermediate product formed is stirred into an aqueous solution of 1&5 kg. betanapthol and 60 kg. of sodium carbonate, made alkaline with soda lye. After a certain time the dyestuff is separated in the usual manner.

The sodium salt of the dyestuff constitutes a brown powder, dissolving in water with a brown coloration and in concentrated sulfuric acid with a red-brown coloration and dyeing wool in an-acid bath yellow-brown tints becoming fast to washing and to light by subsequent coppering and turning on subsequent chromating to a dark brown very ders, which fast to Washing, fulling and potting and to light.

What I claim is: V

1. As new products the herein described azodyestuffs dyeing on mordants, derived from the product of diazotation of the bodies corresponding to the formula bath yellow to blue-violet tints turning on subsequent coppering to greenish-yellow to blue tints fast to washing and to light and on subsequent chromating to yellow to black tints fast to washing, fulling, potting and light.

2. As new products, the herein described azodyestulfs dyeing on mordants, derived from the diazoderivatives of aminoorithooxyarylsulfoarylamids and oxyderivatives of napthalene able to combine with a diazo body, the said dyestuffs constituting in a dry state red-brown to dark colored powdissolve in water with brown to violet colorations and in concentrated sulfuric acid with orange to violet colorations and dyewool in an acid bath red brown to Bordeaux red tints turning. on subsequent chromating to violet-brown to blue tints fast to washing, fulling, potting and li ht.

3. As new product, the herein descri ed azodyestufi' dyeing on mordants and, corre sponding to the formula N=N som soan and resulting from the combination of the diazoderivative of 1-oXy-2-aminobenzene-4 OH OH dm-NH-so/ 'sulfanilid with 1-8-dioxynaphthalene-ii-G- disulfonic acid, the said dyestufi' constituting in a dry state a dark violet powder-dissolving in water andin concentrated sulfuric acid to red-violet solutions and dye wool in an acid bath Bordeaux-red tints turnin on subsequent chromating to blue tints-fast to washing, fulling, potting and light.

In witness whereof I have hereunto signed my name this eighth day of May, 1918, in the presence of two subscribing witnesses.

Witnesses:

' .WAI/inn E. BUNDY,

ARMANI) RETTEY. 

